CN1599734A - 作为cxc趋化因子受体拮抗剂的3,4-二取代的马来酰亚胺化合物 - Google Patents
作为cxc趋化因子受体拮抗剂的3,4-二取代的马来酰亚胺化合物 Download PDFInfo
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022194240A1 (en) * | 2021-03-17 | 2022-09-22 | Biofront Ltd. (Cayman) | Modulators of fpr1 and methods of using the same |
CN115433115A (zh) * | 2022-10-17 | 2022-12-06 | 聊城大学 | 一种3,4-二取代马来酰亚胺类化合物及其合成方法 |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20040106794A1 (en) | 2001-04-16 | 2004-06-03 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
US7132445B2 (en) | 2001-04-16 | 2006-11-07 | Schering Corporation | 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands |
CA2462862A1 (en) | 2001-10-12 | 2003-04-17 | Schering Corporation | 3,4-di-substituted maleimide compounds as cxc-chemokine receptor antagonists |
MXPA04009127A (es) * | 2002-03-18 | 2005-01-25 | Schering Corp | Tratamiento de enfermedades mediadas por quimiocinas. |
JP2005531622A (ja) * | 2002-06-28 | 2005-10-20 | ノバルティス アクチエンゲゼルシャフト | 血管沈静化合物とアルキル化剤を含む腫瘍処置用の組合せ剤 |
PE20040570A1 (es) * | 2002-10-09 | 2004-08-30 | Pharmacopeia Drug Discovery | Tiadiazoldioxidos y tiadiazoloxidos como ligandos del receptor de cxc- y cc-quimiocina |
WO2005012256A1 (en) | 2003-07-22 | 2005-02-10 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
MXPA06007076A (es) * | 2003-12-19 | 2006-08-31 | Pharmacopeia Drug Discovery | Tiadiazoles como ligandos del receptor cxc y cc-quimiocina. |
MXPA06007205A (es) * | 2003-12-22 | 2006-08-31 | Schering Corp | Dioxidos de isotiazol como ligandos del receptor cxc y cc-quimiocina. |
WO2005103711A2 (en) * | 2004-04-20 | 2005-11-03 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with cxc chemokine receptor 1 (cxcr1) |
CN1984899B (zh) * | 2004-05-12 | 2011-07-27 | 先灵公司 | Cxcr1和cxcr2趋化因子拮抗剂 |
SE0500055D0 (sv) | 2005-01-10 | 2005-01-10 | Astrazeneca Ab | Therapeutic agents 3 |
MX2007008370A (es) | 2005-01-10 | 2007-08-21 | Astrazeneca Ab | Derivados de 1,1-dioxidos de isotiazol-3 (2h) -ona como moduladores del receptor del higado x. |
SE0500058D0 (sv) * | 2005-01-10 | 2005-01-10 | Astrazeneca Ab | Therapeutic agents 5 |
US8440217B1 (en) | 2005-06-15 | 2013-05-14 | Mawaheb M. EL-Naggar | Method and system with contact lens product for treating and preventing adverse eye conditions |
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LT1951663T (lt) * | 2005-11-24 | 2016-11-10 | Dompé Farmaceutici S.P.A. | (r)-arilalkilamino dariniai ir juos turinčios farmacinės kompozicijos |
TW200813033A (en) * | 2006-07-07 | 2008-03-16 | Schering Corp | 3, 4-di-substituted cyclobutene-1, 2-diones as CXC-chemokine receptor ligands |
FR2927075A1 (fr) * | 2008-02-04 | 2009-08-07 | Centre Nat Rech Scient | Molecules comprenant un squelette bis-(heteroaryl)maleimide, et leur utilisation dans l'inhibition d'enzymes |
US7943527B2 (en) * | 2008-05-30 | 2011-05-17 | The Board Of Trustees Of The University Of Illinois | Surface preparation for thin film growth by enhanced nucleation |
CN102958927A (zh) | 2010-05-12 | 2013-03-06 | Abbvie公司 | 激酶的吲唑抑制剂 |
CN104334545A (zh) | 2012-03-16 | 2015-02-04 | 埃克希金医药品有限公司 | 3,5-二氨基吡唑激酶抑制剂 |
US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
KR101556276B1 (ko) * | 2012-12-28 | 2015-09-30 | 제일모직 주식회사 | 하드마스크 조성물용 모노머, 상기 모노머를 포함하는 하드마스크 조성물 및 상기 하드마스크 조성물을 사용하는 패턴형성방법 |
US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
NZ631142A (en) | 2013-09-18 | 2016-03-31 | Axikin Pharmaceuticals Inc | Pharmaceutically acceptable salts of 3,5-diaminopyrazole kinase inhibitors |
AR103264A1 (es) | 2014-12-23 | 2017-04-26 | Axikin Pharmaceuticals Inc | Derivados de 3,5-aminopirazol como inhibidores de quinasa rc |
JP2020508436A (ja) | 2016-12-07 | 2020-03-19 | プロジェニティ, インコーポレイテッド | 胃腸管の検出方法、装置およびシステム |
CA3045310A1 (en) | 2016-12-14 | 2018-06-21 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
WO2019044739A1 (ja) * | 2017-08-31 | 2019-03-07 | 国立大学法人京都工芸繊維大学 | 蛍光体及びその利用 |
WO2020106750A1 (en) | 2018-11-19 | 2020-05-28 | Progenity, Inc. | Methods and devices for treating a disease with biotherapeutics |
WO2021119482A1 (en) | 2019-12-13 | 2021-06-17 | Progenity, Inc. | Ingestible device for delivery of therapeutic agent to the gastrointestinal tract |
Family Cites Families (37)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1669798A1 (de) | 1966-07-28 | 1971-08-26 | Huels Chemische Werke Ag | Verfahren zum Stabilisieren markomolekularer Polyacetale |
CS214745B2 (en) * | 1976-08-28 | 1982-05-28 | Huels Chemische Werke Ag | Shaped and non-shaped products from plastic materials |
FI832519L (fi) | 1982-07-12 | 1984-01-13 | Bristol Myers Co | Farmaceutiska foerfaranden och sammansaettningar |
DE3309655A1 (de) | 1983-03-17 | 1984-09-20 | Bayer Ag, 5090 Leverkusen | 1,2,5-thiadiazol-1-oxide und 1,1-dioxide, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
JPS60255756A (ja) * | 1984-06-01 | 1985-12-17 | Ikeda Mohandou:Kk | アミノアルキルフエノキシ誘導体 |
HU198696B (en) | 1987-01-20 | 1989-11-28 | Nissan Chemical Ind Ltd | Process for producing 3/2h/-pyridazinon derivatives and pharmaceutical compositions containing them as active components |
JPH02256668A (ja) | 1988-12-20 | 1990-10-17 | Nissan Chem Ind Ltd | ピリダジノン誘導体 |
US5206252A (en) * | 1992-05-08 | 1993-04-27 | American Home Products Corporation | Thiadiazolyl-amino derivatives of benzopyrans and indanes |
GB9312210D0 (en) | 1993-06-14 | 1993-07-28 | Smithkline Beecham Plc | Chemical compounds |
US5354763A (en) | 1993-11-17 | 1994-10-11 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
US5506252A (en) * | 1993-11-17 | 1996-04-09 | American Home Products Corporation | Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones |
US5466712A (en) | 1994-11-04 | 1995-11-14 | American Home Products Corporation | Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones |
AU686896B2 (en) | 1994-11-16 | 1998-02-12 | American Home Products Corporation | Diaminocyclobutene-3,4-diones |
WO1998032439A1 (en) * | 1997-01-23 | 1998-07-30 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
US5840764A (en) * | 1997-01-30 | 1998-11-24 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
AU6250298A (en) | 1997-01-30 | 1998-08-25 | American Home Products Corporation | Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones |
AR015425A1 (es) * | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol, composicion farmaceutica que los contiene, su uso en la manufactura de un medicamento, procedimiento para su preparacion,compuestos intermediarios y procedimiento para su preparacion |
WO2000020378A1 (en) | 1998-10-02 | 2000-04-13 | Neurosearch A/S | Diaminocyclobutene-3,4-dione derivatives, their preparation and use |
AU6111699A (en) | 1998-10-08 | 2000-05-01 | Smithkline Beecham Plc | Novel method and compounds |
US6376555B1 (en) * | 1998-12-04 | 2002-04-23 | American Home Products Corporation | 4-substituted-3-substituted-amino-cyclobut-3-ene-1,2-diones and analogs thereof as novel potassium channel openers |
JP2002532457A (ja) | 1998-12-14 | 2002-10-02 | アメリカン・ホーム・プロダクツ・コーポレイション | Vla−4により仲介される白血球接着を阻害する3,4−ジアミノ−3−シクロブテン−1,2−ジオン誘導体 |
US6420396B1 (en) * | 1998-12-16 | 2002-07-16 | Beiersdorf Ag | Biphenyl and biphenyl-analogous compounds as integrin antagonists |
EE200100317A (et) | 1998-12-16 | 2002-08-15 | Bayer Aktiengesellschaft | Uued bifenüül- ja bifenüülanaloogsed ühendid kui integriini antagonistid |
US6518283B1 (en) | 1999-05-28 | 2003-02-11 | Celltech R&D Limited | Squaric acid derivatives |
US6586446B1 (en) | 1999-10-15 | 2003-07-01 | Bristol-Myers Squibb Company | Bicyclic and tricyclic amines as modulators of chemokine receptor activity |
WO2001064691A1 (en) | 2000-03-01 | 2001-09-07 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
AR033803A1 (es) | 2000-03-01 | 2004-01-07 | Smithkline Beecham Corp | Compuestos de dianilino escuarano, composiciones farmaceuticas que los comprenden, y el uso de los mismos en la fabricacion de medicamentos para tratar enfermedades mediadas por quimioquinas |
JP2003527360A (ja) | 2000-03-14 | 2003-09-16 | スミスクライン・ビーチャム・コーポレイション | Il−8受容体アンタゴニスト |
CN1454204A (zh) | 2000-05-30 | 2003-11-05 | 史密丝克莱恩比彻姆公司 | Il-8受体拮抗剂 |
AR032398A1 (es) | 2001-01-16 | 2003-11-05 | Smithkline Beecham Corp | Compuesto de escuaramida de sulfonamida, composicion farmaceutica que lo comprende y uso de dicho compuesto para preparar dicha composicion |
US20040132694A1 (en) | 2001-01-16 | 2004-07-08 | Palovich Michael R. | Il-8 receptor antagonists |
AU2002303084B2 (en) | 2001-02-02 | 2006-05-25 | Pharmacopiea, Inc. | 3,4-di-substituted cyclobutene-1, 2 -diones as CXC chemokine receptor antagonists |
US20030204085A1 (en) | 2001-02-02 | 2003-10-30 | Taveras Arthur G. | 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists |
PL207255B1 (pl) | 2001-04-16 | 2010-11-30 | Pharmacopeia Drug Discovery | 3,4-di-podstawione cyklobuten-1,2-diony i ich zastosowanie oraz zawierająca je kompozycja farmaceutyczna |
CA2462862A1 (en) | 2001-10-12 | 2003-04-17 | Schering Corporation | 3,4-di-substituted maleimide compounds as cxc-chemokine receptor antagonists |
US6878709B2 (en) | 2002-01-04 | 2005-04-12 | Schering Corporation | 3,4-di-substituted pyridazinediones as CXC chemokine receptor antagonists |
MXPA04009127A (es) | 2002-03-18 | 2005-01-25 | Schering Corp | Tratamiento de enfermedades mediadas por quimiocinas. |
-
2002
- 2002-10-11 CA CA002462862A patent/CA2462862A1/en not_active Abandoned
- 2002-10-11 EP EP02786395A patent/EP1434775A1/en not_active Withdrawn
- 2002-10-11 US US10/269,775 patent/US6903131B2/en not_active Expired - Fee Related
- 2002-10-11 MX MXPA04003439A patent/MXPA04003439A/es unknown
- 2002-10-11 WO PCT/US2002/032628 patent/WO2003031440A1/en not_active Application Discontinuation
- 2002-10-11 JP JP2003534423A patent/JP2005505595A/ja active Pending
- 2002-10-11 CN CNA028240529A patent/CN1599734A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2022194240A1 (en) * | 2021-03-17 | 2022-09-22 | Biofront Ltd. (Cayman) | Modulators of fpr1 and methods of using the same |
WO2022193187A1 (en) * | 2021-03-17 | 2022-09-22 | Biofront Ltd. (Cayman) | Modulators of fpr1 and methods of using same |
CN115433115A (zh) * | 2022-10-17 | 2022-12-06 | 聊城大学 | 一种3,4-二取代马来酰亚胺类化合物及其合成方法 |
Also Published As
Publication number | Publication date |
---|---|
US6903131B2 (en) | 2005-06-07 |
JP2005505595A (ja) | 2005-02-24 |
CA2462862A1 (en) | 2003-04-17 |
MXPA04003439A (es) | 2004-07-08 |
WO2003031440A1 (en) | 2003-04-17 |
US20040034229A1 (en) | 2004-02-19 |
EP1434775A1 (en) | 2004-07-07 |
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